Web scraping is one of those skills that prints money if you aim it at a real pain point instead of trying to build a product around it.
The fastest money is honestly the boring freelance work. Small businesses and agencies constantly need one-off scrapes: competitor price lists, product catalogs, local business directories for outreach lists, review data for sentiment analysis. A Python + Playwright script that takes you an hour to write can be worth $100-$500 to the right client, and the demand for this is genuinely endless on Upwork and in the Hire a Freelancer section here.
The next level up is recurring data feeds. Price monitoring for e-commerce stores, job board aggregation, real estate listings, inventory alerts. Anything where someone pays monthly to get fresh data without maintaining the scraper themselves. That is where scraping turns from one-off gigs into actual MRR.
One thing I would avoid: the "I'll build an aggregator site and monetize with ads" route. That model has been basically dead since Google started crushing thin affiliate/aggregator sites. Sell the data itself, or sell the service of maintaining the scraper. That is where the margins are.
And respect rate limits and rotate your IPs properly if you want to keep your infrastructure alive. Nothing kills a scraping income stream faster than burned proxies and a cease-and-desist from a site that notices you.